So, I know destination weddings elicit a groan from some guests, but for this travel-and-champagne-addict, it’s a swoon-worthy combination. So when my friend high school friend Liz announced the location for her very own destination wedding, I couldn’t have been more thrilled. It’s a goal of mine to visit all fifty states someday, and with less than half ticked off the list, I do try — and frequently fail — to squeeze in at least one new one per year. Maine has topped the list for years! Turned out that for the summer of 2017, I would finally get there — my twenty-second United State of America.

The wedding was located in Harpswell, Maine, and I originally planned to build a full one or even two week trip around it. Unfortunately, life got in the way and I ended up with just four days — but I was determined to make the most of them. And that involved using as many Maine themed puns as humanely possible.

With my mom as my wedding one and travel buddy, I hopped a flight from Philly to Boston, she swooped up with the car from Martha’s Vineyard, and together we headed north.

Our first stop, after a short swoop through an art gallery in Wells, was Kennebunkport. This little coastal town is famous for being the vacation destination of the Bush family, and as Martha’s Vineyard residents, we do love our destinations steeped in presidential lore. Unabashedly preppy Kennebunkport is a quintessential East Coast destination I just couldn’t miss.

We kicked off our rainy visit with lunch at the fantastic local favorite , overlooking the cloudy harbor. It was incredibly scenic even covered in a coat of gray — I can’t even imagine how quaint it would be on a bright sunny day.

After lunch, I was tempted by a tasting at , which is based in Portland but recently opened their Kennebunkport tasting room. It was a nice mid-day pick-me-up, and I ended up buying a bottle of the Lavender Lemonade and the Habanero Lime.

Before heading out of town, we did one lap of the charming town center shops. I treated myself to a pair of Sperry’s tennis shoes and a slice of fudge, classic New England purchases.

Eventually, we said a reluctant goodbye to Kennebunkport and made our way up to South Freeport to check into our highly anticipated Airbnb. I admit that when I started researching this trip, one of the things that prevented me from extending it was the cost of Maine’s accommodation in the summer.

Prices were shockingly steep, even for fairly nondescript motels in the rural area around the wedding venue. I suppose with a very limited warm weather window, hoteliers have no choice but to make hay while the sun shines — literally. Airbnb to the rescue!

For cheaper than even the wedding rate at the local Best Western, we scored on the property of the sweetest local couple. The wife is a clothing designer who imports fabrics from Bali, and the husband teaches Tai Chi lessons in the barn when they don’t have guests. He left us little treats like fresh strawberries and local chocolates every day, and was incredibly helpful in doling out recommendations for the area. They even recycled and offered to compost any food waste we produced — so sustainable!

Freeport itself is really known as more of a retail center — it has the world’s first and largest LL Bean, which is open 24/7 and where we had a great breakfast in the cafe! — but South Freeport has a more charming, rural feel.

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That night, we hopped back in the car to head to in Brunswick. We were pretty tired from a long day behind the wheel and considered sticking closer to home, but as soon as we arrived at Frontier we knew the twenty minute drive had been well worth it.

This gallery, theater and restaurant was the kind of place I like to think I’d be a regular if I were a Brunswick resident — organic, locally sourced healthy meals, screenings of documentaries and indie films, and shows by local artists. Plus, killer sunset views — and the waitress genuinely thanked me when I asked for no straw in my water (a kindred single-use plastic loather!) It might have been one of my favorite meals in Maine, and there was a lot of competition.

The next morning, we woke up bright and early to walk the four minutes from our Airbnb to the Harraseeket Harbor. While the rest of the day would be taken up by bridesmaid duty in Portland, it was nice to kick things off with another peek at charming, small town coastal Maine. The harbor was deserted but for a few fishermen in the early morning hours, though my mom told me when she returned later for lunch the line for lobster was wrapped around the building.

This two day wedding extravaganza was special enough to warrant a post of it’s own — so stay tuned for that. For now, we’ll fast forward to our fourth and final day in Maine, which arrived all too quickly.

We were sad to say goodbye to our adorable Airbnb — but I was pretty thrilled to be rocking day-after wedding braid.

We’d decided to spend the day in Portland but made a quick detour when we saw a sign for DeLorme mapping, home of Eartha. Eartha is the world’s largest rotating and revolving globe, conveniently located right on our path of travel in Yarmouth, Maine. What travel blogger could possibly pass by without stopping?!

Unfortunately it was a Sunday and so the building was closed — but we managed to admire it just fine from the outside.

Next stop, brunch at . Portland, Maine, much like its West Coast namesake, is known for it’s insanely high quality restaurant scene. We were so hungry we inhaled our beautiful entrees — including a pulled pork breakfast burrito with local peaches, and a fried chicken and biscuit sandwich — before I had the chance to snap a photo.

Bad blogger, but great burrito. So far, Portland was really living up to its reputation, and I can’t recommend Hot Suppa more highly if you’re in the area.

Next, we drove down to the harbor area to stroll around, do a bit of gift shopping, and get a feel for Maine’s largest city. Portland was nothing like I expected Maine to be — Kennebunkport was more the vision I had in my head for the Pine Tree State (which also, in my opinion, could work on its official state nickname.)

But while Portland was more modern than I expected, even after our short trip I agreed with assessment of it as “one of the hippest, most vibrant small cities in America.”

Leaving Portland proper, we headed out on a mission to tick off two final Maine must-dos off our bucket list: blueberry ice cream and lighthouses. While there had been plenty of ice cream opportunities in Kennebunkport, our first two days were pretty chilly — this was really our first beautiful sunny day of exploration.

First up, Bug Light. Bug Light Park was just moments outside Central Portland and offered gorgeous views of the city’s skyline. With kites blowing in the breeze, residents relaxing on quilts and lawn chairs and sailboats dancing in the harbor, it would be hard to paint a more idyllic scene. A World War II Memorial in one corner was a touching tribute.

Next up, Portland Head Lighthouse in Fort Williams Park. Be careful if you’re headed here — though it’s alleged to be the most photographed spot in Maine and shouldn’t be too tricky to find, we almost got tricked by a Google Map error that marked it at a different location in Cape Elizabeth.

Thankfully, we followed our instincts and found the iconic lighthouse, which was every bit as impressive as its reputation promised.

And then, in what felt like the blink of an eye, we were on our way back to the New Hampshire border, starting our four-state crawl back to New York.

Our time in Maine really was fleeting, though we managed to at least glance at several of Southern Maine’s most enticing destinations — charming Kennebunkport, quirky Portland, rustic Harpswell, sweet South Freeport, and crunchy Brunswick. While the major destinations of the North were calling to me — Acadia National Park, I’m dying to camp in you! — I’m quite certain this won’t be my last jaunt to Maine.

Gosh, I love Maine so much! I spent a few days in Bar Harbor and Portland last year and it was the best. We missed out on Hot Suppa sadly, but definitely enjoyed the food scene in Portland. I think if I had to pick a place to “summer” it would definitely be somewhere in Maine.Kacy recently posted..

So glad that you love Maine! It’s the best, but, of course, I’m biased. Acadia National Park is worth it so put it on your calendar for next summer! That’s funny that your GPS almost sent you somewhere else in Cape for the lighthouse. Portland Head is actually the most photographed lighthouse in the United States! Hot Suppa is pretty awesome. I live right around the corner from it. And these are tons more amazing options to try when you come back.

I’d love to visit Maine & like you, find weddings one of the best excuses to explore new states & beyond. I’ve got some South Carolina nuptials coming up in March & then a Bali wedding next summer. Cannot wait!!!

I need friends to start getting married so I can travel to their weddings xD I’m not quite old enough where that’s really started happening yet lol. But dude this post is awesome, I really really want to visit Maine! It has my perfect kind of weather and from what I’ve heard about it the towns are just the kind I love visiting. Perhaps the accommodation prices would be better in the spring or fall, you think? Because I am both cheap and completely fine with chilly weather 😀

I have a thing for Maine. A bit of an obsession really. I have loved Stephen King’s books (most of which take place in his home state Maine), since I was a little girl. So, Maine has been in my head since then.

There are areas of the States I’m more eager to check out first, but New England is quite close to the top of my wishlist!Dominique recently posted..

If I were to rank all the states I have yet to visit based on my desire to see them, Maine would probably be somewhere around the middle. Still, I love that it seems to have so many cities that are so quaint! Kennebunkport in particular looks adorable, and sort of reminds me of Peggys Cove in Nova Scotia.Marni recently posted..

I have yet to visit Maine but it has been on the list forever! I love that photograph of the women drinking wine. It sounds like you had a fun trip and I will be bookmarking this for when I finally make my way up there 😀Chanel | Cultural Xplorer recently posted..

I am another person who has not been to Maine yet, but really longs to see this. I have this vision of the small coastal towns being similar to British coastal towns, and being the “way the US was supposed to look.” I am not sure where it comes from, but must get a visit onto an itinerary soon… Bookmarking for when I start those plans!Roxanna recently posted..

I'm a New York native who left my home to explore the world slowly and thoroughly. I’m just a little obsessed with photography, scuba diving, and reading guidebooks to countries I have no immediate plans to visit.